N-Biphenyl-2-yl-2-chloro-acetamide → 5H,7H-Dibenzo[b,d]azepin-6-one

HRID 2105890

Reaction equation

[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:15])[CH2:13]Cl>ClC1C=CC=C(Cl)C=1>[CH:10]1[C:5]2[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:13][C:12](=[O:15])[NH:11][C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 170 °C

Procedure

AlCl3 (12.1 g) was added to a solution of N-biphenyl-2-yl-2-chloro-acetamide (9.9 g) in 1,3-dichlorobenzene (99 mL). The reaction mixture was stirred for 24 hours at 170° C., cooled to 0° C. and poured into ice-water (1500 mL). The suspension obtained was filtered off, the precipitate washed with water (250 mL), 2 portions of hexane/dichloromethane 4:1 (25 mL), 2 portions of water (125 mL) and 2 portions of hexane (25 mL) affording 5H,7H-dibenzo[b,d]azepin-6-one (6.9 g, 82.5%) as an off-white powder.

Workup

temperaturecooled to 0° C.
customThe suspension obtained
filtrationwas filtered off
washthe precipitate washed with water (250 mL), 2 portions of hexane/dichloromethane 4:1 (25 mL), 2 portions of water (125 mL) and 2 portions of hexane (25 mL)

Sources & evidence

ORD record: ord-7aa0953984eb43d0a97d4253625c4f01
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579464B2

Linked notes

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